Water → HCID 12701049, compound

HRID 127292Notes

Reaction equation

HRID 127292 reaction equation
[C:1]([OH:8])(=O)[CH2:2][CH2:3][C:4](O)=[O:5].[NH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.CS(O)(=O)=O.O>C1(C)C(C)=CC=CC=1>[N:13]1[CH:14]=[CH:15][C:10]([N:9]2[C:4](=[O:5])[CH2:3][CH2:2][C:1]2=[O:8])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1110Succinic AcidHCID 17274-AminopyridineHCID 6395Methanesulfonic Acid

Product 1

HCID 12701049HCID 12701049, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The starting material is prepared as follows: The mixture of 500 g of succinic acid anyhydride, 471 g of 4-amino-pyridine and 5,200 ml of xylene is heated to reflux while stirring and separating the water formed. After 30 minutes 15 ml of methane sulfonic acid are added and refluxing is continued until 5 moles of water are collected, requiring about 4 days. The mixture is cooled to room temperature, the supernatant is decanted off and the suspension combined with 1000 ml of isopropanol. It is stirred for 5 minutes, filtered, the residue washed with 250 ml of isopropanol and dried for 3 days under reduced pressure at room temperature and shortly at 50° , to yield the 1-(4-pyridyl)-pyrrolidin-2, 5-dione melting at 232°-235° .

Workup

  1. customThe starting material is prepared
  2. temperatureto reflux
  3. customseparating the water
  4. customformed
  5. temperaturerefluxing
  6. customare collected
  7. customthe supernatant is decanted off
  8. stirringIt is stirred for 5 minutes
  9. filtrationfiltered
  10. washthe residue washed with 250 ml of isopropanol
  11. customdried for 3 days under reduced pressure at room temperature and shortly at 50°

Sources & evidence

ORD record
ord-aef3579365064843ba923a6a9f15eb6e
Source dataset
uspto-grants-1981_03
Patent number
US04255429

Reaction notes

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